Human Metabolome Database: Showing metabocard for Proline betaine (HMDB0004827)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-08-24 14:41:17 UTC

Update Date

2020-02-26 21:25:15 UTC

HMDB ID

HMDB0004827

Secondary Accession Numbers

HMDB04827

Metabolite Identification

Common Name

Proline betaine

Description

Proline betaine, also known as stachydrine or dimethylproline, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Proline betaine is a biomarker for the consumption of citrus fruits. Proline betaine is a moderately acidic compound (based on its pKa). Proline betaine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Proline betaine is found, on average, in the highest concentration within capers. Proline betaine has also been detected, but not quantified in, several different foods, such as spelts, sweet oranges, annual wild rices, oats, and tartary buckwheats. This could make proline betaine a potential biomarker for the consumption of these foods. Elevated levels of proline betaine in human urine are found after the consumption of citrus fruits and juices (PMID: 18060588 ). Proline betaine is a glycine betaine analogue found in many citrus foods. Proline betaine is an osmoprotective compound found in urine. It is thought to serve an osmoprotective role for the kidney.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Carboxylato-1,1-dimethylpyrrolidinium	ChEBI
N,N-Dimethyl-L-proline	ChEBI
Stachydrine	ChEBI
L-Proline betaine	Kegg
Dimethylproline	HMDB
Stachydrine chloride, (S)-isomer	HMDB
Stachydrine chloride	HMDB
Stachydrine, (+-)-isomer	HMDB
(2S)-2-Carboxy-1,1-dimethylpyrrolidinium	HMDB
(S)-2-Carboxy-1,1-dimethylpyrrolidinium	HMDB
Homostachydrine	HMDB
Prestwick-08g03	HMDB
Proline betaine	ChEBI

Chemical Formula

C₇H₁₃NO₂

Average Molecular Weight

143.1836

Monoisotopic Molecular Weight

143.094628665

IUPAC Name

(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

Traditional Name

stachydrine

CAS Registry Number

471-87-4

SMILES

C[N+]1(C)CCC[C@H]1C([O-])=O

InChI Identifier

InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1

InChI Key

CMUNUTVVOOHQPW-LURJTMIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
L-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
N-alkylpyrrolidine
Tetraalkylammonium salt
Pyrrolidine
Quaternary ammonium salt
Carboxylic acid salt
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organic salt
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

amino-acid betaine (CHEBI:35280 )
alkaloid (CHEBI:35280 )
N-methyl-L-alpha-amino acid (CHEBI:35280 )
Pyrrolidine alkaloids (C10172 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Source:

Biological:

Plant:

Fabaceae

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Osmolyte

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.67 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.11 m³·mol⁻¹	ChemAxon
Polarizability	15.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-9000000000-36bbb91342358293711a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-ea4782d2282bc28329c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-4900000000-75a3b0df6adc0100b9fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9000000000-5df24b6079668b584f79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-34921bec4b2fad07f505	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-3900000000-da3a14fcb5a4909b775e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-7b04a861eee46ac86b66	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	10.0 (0.0-50.00) uM	Adult (>18 years old)	Both	Normal	8068711	details
Blood	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified		Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified		Adult (>18 years old)	Female	Normal	27355821	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	22727327	details
Urine	Detected and Quantified	2.3 (0.8-4.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	20573794	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	20573794	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	23269817	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	23425595	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	23657156	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24390407	details
Urine	Detected and Quantified	12.7 (1.645-23.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3546377	details

Abnormal Concentrations

Biospecimen	Status	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Blood	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB04284

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7089

PubChem Compound

115244

PDB ID

Not Available

ChEBI ID

35280

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Le Rudulier D, Bernard T, Goas G, Hamelin J: Osmoregulation in Klebsiella pneumoniae: enhancement of anaerobic growth and nitrogen fixation under stress by proline betaine, gamma-butyrobetaine, and other related compounds. Can J Microbiol. 1984 Mar;30(3):299-305. [PubMed:6372974 ]
Chambers ST, Kunin CM: Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731-7. [PubMed:3546377 ]
Lever M, Sizeland PC, Bason LM, Hayman CM, Chambers ST: Glycine betaine and proline betaine in human blood and urine. Biochim Biophys Acta. 1994 Aug 18;1200(3):259-64. [PubMed:8068711 ]
Atkinson W, Downer P, Lever M, Chambers ST, George PM: Effects of orange juice and proline betaine on glycine betaine and homocysteine in healthy male subjects. Eur J Nutr. 2007 Dec;46(8):446-52. Epub 2007 Dec 4. [PubMed:18060588 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Proline betaine (HMDB0004827)

Structure for HMDB0004827 (Proline betaine)